Reactions of Sulfonate and Sulfate Esters

Abstract

This chapter is organized on the basis of a classification of sulfonate and sulfate esters according to the nature and number of the alcohols from which they are derived. In the case of the sulfate esters, the reason for this mode of organization is obvious. However, in treating the chemistry of the sulfonate esters, we could have used the nature of the parent sulfonic acids as the basis for the organization of our discussion. We did not do this for two reasons. One is that we wished to present a reasonably parallel treatment of the chemistry of sulfonate and sulfate esters. The other is that we felt that, from a mechanistic standpoint, reactivity patterns emerge most clearly when the reactions of sulfonate esters are examined in terms of the kinds of alcohol groups which can be displaced.

In DMSO, a pKa of 15.6 was found for the ionization of the methylene group in the five-membered sulfone. This value is significantly lower than that measured for the corresponding ionization in phenyl Of-toluenesulfonate. D.F. Mayers, Ph.D. thesis, University of Chicago (1973).Google Scholar